JPS63117031A - Advance epoxy resin, thermosetting composition thereof and curable composition obtained therefrom - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention [Industrial Field of Application] The present invention provides an advanced resin (a
advanced resins).

[Prior art and problems to be solved by the invention] A relatively low-molecular compound that becomes a relatively high-molecular, high-melting-point epoxide resin by reaction with a polyfunctional compound that has many functional groups that react with epoxide groups. ``Advancement'' of low melting point epoxide resin
) are known. Such so-called advances are specifically aimed at improving or modifying the industrial processing properties in the desired direction for a certain end use. For certain end uses, it may be desirable to increase the softening point or melting point, for example in sintering powders, compacting powders, etc.

[Means for solving problems]

The subject of the present invention is (11th formula: % formula % [wherein R represents a phenylene group or a naphthylene group, or one or two carbon-carbon bonds, an ether oxygen atom, a sulfur atom, a sulfonyl group] , represents a group consisting of two or three phenylene groups connected by a sulfoxide group, a carbonyl group, or an alkylene group having 1 to 5 carbon atoms, or each of 1 or 2 monocyclic or multiple rings each phenylene group or each naphthylene group substituted by a C 1 -C 4 alkyl group or by 1 or 2 chlorine or bromine atoms, and R1 is independently C 1 -C 4 alkyl; 16 straight-chain or branched alkyl groups, straight-chain or branched-chain alkyl groups having 1 to 16 carbon atoms substituted with 1 to 4 chlorine or bromine atoms, straight-chain carbon atoms 2 to 6 alkyl groups; or a branched alkenyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 4 chlorine atoms or bromine atoms, a phenyl or naphthyl group, one monocyclic or multiple ring or by two chlorine atoms or bromine atoms or by one or two carbon atoms each having 1 to 4 carbon atoms
and in total from 6 to 12
phenyl or naphthyl, phenylalkyl or naphthylalkyl groups having 1 to 4 carbon atoms, monocyclic or multiple rings having 1 or 2 chlorine or bromine atoms or 1 to 2 carbon atoms; and the phenylalkyl or naphthylalkyl group has a total of 7 to 12 carbon atoms)
a diglycidyl ether of a di-secondary alcohol represented by It is an advanced epoxy resin obtained from reaction with dihydric phenol.

Preferably, each R1 group is identical and each represents an alkyl group having 1 to 14 carbon atoms, an allyl group, a cyclohexyl group or a benzyl group. More preferred compounds are those in which R is an alkylene group having 1 to 4 carbon atoms;
It is a compound that represents a group formed by two phenylene groups connected at the o/-1O9p'- or p, p'-positions. R represents a group of the formula: in which R2 represents a methylene group or an inpropylene group, and each R1 represents an alkyl group having 1 to 12 carbon atoms, in particular 1 to 6 carbon atoms; Compounds are particularly preferred.

Examples of diglycidyl ethers include in particular: 2.2-bis(p-(3-butoxy-2-glycidyloxyprobyloxy)phenyl)propane; 2.2-bis(p-(3- 2.2-bis(p-(3-ethoxy-2-glycidyloxyprobyloxy)phenyl)propane; 2.2-bis(p-(3 -dodecyloxy-2-glycidyloxyprobyloxy)phenyl)-propane; 2,2-bis(p-(3-tetradecyloxy-2-glycidyloxyprobyloxy)phenyl)-propane; 2,2-bis (p-(3-benzyloxy-2-glycidyloxypropyloxy)phenyl)-propane; bis(p-(3-butoxy-2-glycidyloxypropyloxy)phenyl)methane; 1,3-bis(3-7
2-bis(p-(3-butoxy-2-glycidyloxypropyloxy)phenyl)sulfone; 2,2-bis(p-
(3-Cyclohexyloxy-2-glycidyloxypropyloxy)phenyl)-propane; 2.2-bis(4-(3-butoxy-2-glycidyloxypropyloxy)3.5-dibromophenyl)-propane; 2 .2-bis(p-(5-allyloxy-2-glycidyloxypropyloxy)phenyl)-propane; 2.2-bis(p-(5-benzyloxy-2-glycidyloxypropyloxy)phenyl)-propane; 1.3-bis(2-glycidyloxy-3-7enoxypropyloxy)benzene: and 2.2-bis(p-(
3-phenoxy-2-glycidyloxypropyloxy)phenyl)-propane.

Applicable diglycidyl ethers of di-secondary alcohols, processes for their preparation and curable compositions thereof as blends with epoxy resins are disclosed in US Pat. No. 4,284,574.

Applicable dihydric phenols are represented by the following formula % [wherein, X is a 1.2-7 enylene group, a 1.3-phenylene group, a 1. 4-phenylene group or These represent, for example, bisphenol F, A and S1 catechol, resorcinol, o, o'-biphenol and p, p'-biphenol. In various types of phenols, each phenyl group may be substituted with a non-reactive substituent such as a norogen atom or an alkyl group. Bisphenol A is preferred.

The diglycidyl ether of secondary alcohol is 70 to 95, preferably 75 to the advanced resin.
It is generally present in a concentration range of 90% to 90%.

Accordingly, the dihydric phenol is present in a concentration range of 30 to 5 weight percent, preferably 25 to 10% by weight of the advanced resin. Each concentration of 1j is selected to ensure the appropriate molecular weight of the advanced product.

The reaction procedure, the advancement reaction, is known to those skilled in the art and is based on atpansong catalysts (advanc
ing catalyst) or accelerator (acce-
This generally involves the reaction of a diglycidyl ether with a dihydric phenol in the presence of a dihydric phenol.

Typical promoters include alkali metal hydroxides, imidazoles, phosphonium compounds, and the like. The choice of catalyst is specific depending on the intended end use. Preferably, the diglycidyl ether is warmed to about 90° to 120°C to facilitate the initial compounding operation and then the dihydric phenol is added. When stirred in this manner, a clear molten blend is obtained. The advancement reaction then occurs when a catalyst is added and the temperature is raised to 130-180°C. Using samples taken during the reaction, the progress of the reaction can be monitored by titration of epoxide groups. The reaction to yield a resin system having an epoxy value in the range of 001 to α2 epoxy equivalents per resin 1007 is generally completed in 2 to 15 hours. The resulting advanced resin is a viscous liquid or a tacky solid.

After curing, these advanced resins serve as high solids paints and adhesives.
Flexibility, chemical resistance, salt fog immersion needle resistance (5alt fog
enhance the performance properties of the cured product in terms of corrosion resistance) and mechanical properties including hardness, impact strength and mechanical strength.

Depending on the desired end use, the advanced resin is formulated with appropriate ingredients and mixed with appropriate curative and accelerator ingredients. In the first field of application of the resin system as a coating, melamine-formaldehyde hardeners are preferred. Other usable hardeners include di- or polyfunctional incyanates, urea-formaldehyde resins, phenol-formaldehyde resins, and other conventional hardeners.

An effective amount of curing agent is used. The proportions depend on the chemical nature of the curing agent and the desired properties of the curable composition and its cured product, and optimum proportions are readily determined by methods well known in the art. For example, curing agents are used in concentrations ranging from 5 to 20% by weight of the total advanced resin.

The resin-curing agent system can be further mixed with conventional modifiers such as extenders, fillers and reinforcing agents, pigments, dyes, plasticizers, diluents, accelerators, etc. at any stage before curing.

As examples of extenders, reinforcing agents, fillers and pigments which can be used in the curable system according to the invention, the following may be mentioned: coal tar, picemen, glass fibers, boron fibers, carbon fibers, cellulose, polyethylene. powder,
Polypropylene powder, mica, asbestos, various quartz powders, fused silica, silicates, silanes, magnesium and calcium carbonate, gypsum, bentone, silica aerogel (Aerosil [Co.]), lithopone, barite,
Titanium dioxide, carbon black, graphite, iron oxide, or iron powder. Other conventional additives, such as flame retardants such as antimony trioxide, chirotropy agents, flow control agents such as silicones, cellulose acetate butyrate, polyvinyl butyral wax or stearates (some also as mold release agents) ) can also be added to the curable system. The promoters added may be the same as the advancement catalyst, or may further include boron trifluoride monoethylamine complexes, tertiary amines, and the like.

The curable mixture can be produced in a conventional manner using known mixing equipment (stirrers, mixers and rollers).

Curing is generally carried out within a temperature range of 175° to 225°C. As used herein, the expression "curing" refers to a cure to obtain a shaped article, such as a cast, pressed or laminate article, or to give a two-dimensional structure, such as a paint, enamel or adhesive. Together with shaping, it is shown that the adduct and epoxide material are converted into an insoluble and infusible crosslinked product.

Curable epoxide resin mixtures are used in surface protection, electrical industry,
It is particularly useful in the field of laminated processing and construction industry. They are formulations tailored in each case to a specific end use;
Unfilled or filled, optionally in solution or emulsion form, paint enamels, sintered powders, compression molding compositions, dipping resins, filling resins, injection molding compounds, impregnating resins and adhesives. As resin for tools, laminated resin,
It can be used as a binder in sealing and filling compositions, floor covering compositions and mineral aggregate reservoirs.

First and foremost among these is its use as a protective coating. The coating composition can be prepared by spraying, dipping,
It can be applied to any suitable substrate by any suitable means such as buffing, veining or rolling. After application to the desired film thickness, it is cured at room temperature or elevated temperature. The resulting cured coating is porous and has excellent physical properties and chemical resistance. The significant advantages of these systems are illustrated above in the section describing their excellent mechanical properties. Of particular value is the
Unexpectedly low viscosity compared to standard bisphenol A/epichlorohydrin resins. This lower viscosity reduces its solvent emission level for high solids paint formulations,
Environmental Protection Agency
ction agency) regulations. Coatings based on such resins are therefore also unexpectedly highly resistant to salt fog erosion and are characterized by superior adhesion and flexibility over standard bisphenol A resins.

[Examples, effects of the invention]

Hereinafter, aspects of the present invention will be explained in more detail with reference to Examples. In these examples, all parts represent parts by weight unless otherwise specified.

Example! 2 This example shows a typical method for producing an advanced resin of the present invention.

Diglycidyl ether, bisphenol and catalyst were mixed with a mechanical stirrer, condenser and thermometer/The-rmowat
eh ■ Four-necked leakage reactor (4-
neck break-away reaction
kettle). The system with nitrogen gas
After flushing for 0 minutes, the mixture is gradually heated through a heating mantle to the desired reaction temperature. The heating time is 130°C for 2 hours and then 180°C until the resin reaches the theoretical epoxy content specifications.

deflagration 5poon
) and periodically remove samples from the reaction kettle using benzyl alcohol/improper tool (7) 1:1.
Dissolve the mixture in 50id and gently reflux. Add 1 freshly prepared potassium iodide solution (35'
Add 15d water) & Od along with 10 drops of α04 Tibromov Nor Blue solution.

The resulting mixture was then heated under reflux in 1. Titrate with ON standard hydrochloric acid to a slightly yellow end point. Once the epoxy value is within specifications, heating is discontinued and the resulting molten epoxy resin is poured into a lined tray and allowed to solidify.

The following advanced resins are manufactured.

A B CD Bisphenol A 100 200
265 293 (Catalyst) Final epoxide equivalent / 488 862 17
54 2703 Resin type *14 79 *Soft example of repeating unit in resin chain■ Example! The advanced resin obtained in step 2 is blended into the curable coating system as shown below.
0 parts - 1:1:1 methyl ethyl ketone/n-butanol/xylene, 55 wt% solids); alkylated melamine-formaldehyde crosslinked resin Cym from American Cyanamid.
e 1303 (1,87 parts); para-toluenesulfonic acid (PTSA) catalyst (α 183 parts): and 1:1:1 methyl ethyl ketone/n-7'tanol/xylene (1
Part 6).

It is shown as follows.

Hardener Cymel 503 resin/hardener ratio 90:10 solids content is Aal 5 The compound was drawn as an 8 mil wet film on cold rolled steel and incubated at 25°C for 60°C with a 5 minute induction period. Dry with nitrogen for minutes and then cure at 200° C. for 20 minutes. The obtained film exhibits the following properties.

Advanced Resin B CD Appearance Transparent Transparent Transparent Smooth Smooth Smooth Glossy Glossy a Thickness mil: mls) 1.5 to 1.751.
5-2.5 1.25-2.5 Bern (Persoz)
(seconds) 72 309 274 Direct impact (3・Union) 1B4 74.8 69 Back impact (Bei・Union) 184 2a8 184 Pencil hardness 3B 3HF adhesion (%+
100 100 100a) Dry film weight b) ASTM D 4366 (ASTM = American Society for Testing and Materials) c) ASTM G 14 d) ASTM G 14 e) ASTM D 5563 f) ASTM D 3359 g) ASTM G 10 Example ■ Stirring Machine, reflux condenser and thermometer / Thermo -
Other advanced resins are made by placing the reactants in a 2L four-necked leak flask equipped with a temperature regulator.

The reactants are warmed to 180° C. and maintained at this temperature until the predetermined epoxy number is reached.

FG Rohan Bisphenol A 200 26
5 300 formylmethyltriphenylphosphonium chloride (catalyst) [151,52
,0 reaction time (hr) aO14,01
4,0 Final engineering poxy value (equivalent/10 [H') α115
α062 α037 Gardner color
2～3 6 6 Resin type 4
7 9 Example ■ Instead of Cymel 303, various R
Example ■ Gold is repeated except using esimene ■. The formulation is as follows.

Advanced resin (30 parts - 1:1:1 (7) in methyl ethyl ketone/n-butanol/xylene, solid content 55
Weight %) Resimene'741 (21 parts-IkO/:
/-AZ, solid content 87 parts) Resimene"747 (1,87 parts) Resim
ene■797 (2 (11 parts - in ethanol, solid content 9
1% by weight) PTSA (1183 parts) 1:1:1 methyl ethyl ketone/n-butanol/xylene 741 (15,35 parts) 747 (15,557 parts) 797 (15,420 parts) Resin/hardener ratio 90:10 solid fraction is 3ELj5 A fill produced in the same manner as in Example ① exhibits the following properties.

Advanced resin EFG appearance
Transparent Transparent Transparent glossy Shiny glossy smooth Smooth Smooth (smooth) 1.5-10 10-2.5
1.5-2.5 pesos (seconds) 107
170 213 Direct impact (cm-kf) 1
84 1114 184 Rear side impact (mouth/leg)
184 184 184 Lead Princess Hardness F
HB 2B adhesive strength (chi) 10
0 100 100 mandrel bending Pa5s
Pa5s Pa5scL36n[13t-1n
α3σ Advanced Resin E
G Appearance Transparent
Transparent glossy glossy ripple-like ripple-like thick mill) 1.5-2.0 2
．． 25-45 Bern (seconds) 139
540 Direct impact (cm-kp) 184
10A5 back impact (c!n-yang) 18
4 57.5 Pencil hardness 2H2H Contact force (%) 100 100 Advanced Jugetsu EFG appearance
Transparent Transparent Clear glossy Shiny Shiny smooth Smooth Smooth (thick mil) 1.5-2.2 1.845
1.6-2.2 pesos (seconds) 47 1
92 302 Direct Impact (c!n-gin) 8&2
5 184 184 Back impact (cln-kf) 126
．． 5184184 Pencil hardness 2B F
2J (Adhesive strength (%) 100 10
0 100 Examples ■ The indicated catalyst was trifluoromethanesulfonate catalyst FC-520 manufactured by 3M Co.:
Advanced Resins E, F, and G are reproduced as described in Example 2, except that 1.5 parts are substituted. The resulting advanced resins are designated H, I and J, respectively, and have 4.7 and 9 repeat units in the resin chain.

CIBA-GEIGY Crop,
) phenol formaldehyde condensate crosslinked am fat H
2949-U with methyl ethyl ketone solvent.
% by weight (non-volatile) solution, resin-curing agent ratio 3:1
Each of the Advanced Resins H, 1 and J is formulated into a curable coating system according to the procedure of Example 2 except for use in Example 3.

Next, the viscosity of the resulting resin system was measured using a B-type viscometer (
Brookf 1eld Viscometer)
The following results are obtained.

Advanced resin HIJ Resin solution viscosity (Cps) 100 100 10
Non-volatile content required to obtain resin solution of 01000 cps 70 70
70 All resins (non-volatile matter) 656 656
It can be seen that the advanced resins of the present invention can be formulated into desired isolid-based formulations.

Example ■ The advanced resin formulation prepared in Example ■ was drawn as a 6 mil wet film on cold rolled steel and
Dry at 200°C for 30 minutes, then cure at 200°C for 20 minutes.

These films exhibit the following properties:

Advanced Resin) TIJ Appearance Transparent Transparent Transparent Smooth Smooth Smooth Thickness Mil) 2 2 2 pesos (seconds)
209 320! +30 direct impact (
cm-kf) 184 184 184 Back impact (cm-kf) 53 46 S
2 Pencil hardness 2H2H2H Adhesive strength (chi) 100 100 100
Thus, these data demonstrate that the advanced resins of the present invention have excellent mechanical properties, particularly adhesion, flexibility, and high direct impact resistance.

Example ■ The surface protection performance of the advanced resin of the present invention was evaluated by a salt fog corrosion test (5alt Fog Corrosion Te5t).
). This test is ASTM B1
17-75 and consists of exposing the specimen to steam from a 5% by weight saline solution. The test specimens are painted steel panels manufactured above. Apply tape to both unpainted and painted surfaces to prevent moisture from seeping under the paint.

"Non-destructive" measurements are carried out at periodic intervals to determine the degree of rust occurrence (none, small, medium, dog) and the appearance of blisters.
r) Visual observation of the surface of the exposed panel to determine the amount and nature of the occurrence (according to ASTM D714...indicated as "F" = dilute M" = moderate, "D" - rich...) White blisters generally indicate the presence of water, while black blisters generally indicate edge regions and other decomposition products.

The ``creepage'' distance, or etching mark (e
Delami Seal (delami) from tchmark
nation) and record surface conditions.

The results are as follows.

Series 1 Curing agent - CYMEL ■ 301 (Alkylated melamine-formaldehyde resin manufactured by American Cyanamid) Resin: Curing agent ratio - 9:1 Curing conditions - 20 minutes at 200°C Exposure time - 864 hours H82M (black) Small I 92FC black) small J
9 2MD (black) Small series 2 Hardening agent - Hz949-U (manufactured by Civer Geigy above)
Resin: hardener ratio - 3 = 1 Curing conditions - 20 minutes at 200°C Exposure time - 864 hours) 1 6 2F (black) Small I 6 8F (black) Medium 7
6 8F (black) Medium series 3 Hardening agent - CYMEL 300 (manufactured by Abakan Cyanamid) Resin: hardening agent ratio - 9:1 Curing conditions - 20 minutes at 200°C Exposure time - 864 hours H52F (black) Small I 4 2M (black)
Small 6D (white) Series 4 Hardening agent - CYMEL 303 (manufactured by American Cyanamid) Resin: hardening agent ratio - 9:1 Curing conditions - 20 minutes at 200°C Exposure time - 864 hours H152F (black) None 1 7 2F ( black) small J
5 6M (black) Small series 5 (same as series 4 except that CYMEL 350 hardening agent is used) J 8 2F (black) Small series 6 Hardening agent - BECKAMINE 2l-511 (butylated urea manufactured by Monsando Chemical) Formaldehyde resin) Resin:hardener ratio - 77:23 Curing conditions - 15 minutes at 177°C Exposure time - 1200 hours 8 10 2F (black) This data provides a general indication of the improved erosion resistance performance of the advanced resin portion of the present invention. It shows a pattern.

In summary, it can be seen that the present invention provides an advanced resin system resulting in a cured composition exhibiting improved performance properties.

The blending proportions, operating procedures, and materials may be changed without departing from the scope of the present invention.

Claims (12)

[Claims] (1) (i) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a phenylene group or a naphthylene group, or one or two carbon-carbon bonds, an ether oxygen atom, Sulfur atom, sulfonyl group, sulfoxide group,
Represents a group consisting of two or three phenylene groups connected to a carbonyl group or an alkylene group having 1 to 5 carbon atoms, or a group consisting of 1 or 2 monocyclic or multiple rings each having 1 carbon atom by 1 to 4 alkyl groups or 1 or 2
each phenylene group or each naphthylene group substituted by chlorine or bromine atoms, and R^1 is independently a straight-chain or branched alkyl group having 1 to 16 carbon atoms, 1 to 4 carbon atoms; straight-chain or branched-chain alkyl groups having 1 to 16 carbon atoms substituted with chlorine or bromine atoms, straight-chain or branched-chain alkenyl groups having 2 to 6 carbon atoms, 1 to 4 chlorine atoms or a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, phenyl or naphthyl group, monocyclic or multiple rings substituted with bromine atoms, with one or two chlorine or bromine atoms, or one or substituted by two C1 -C4 alkyl groups and in total 6 to 1
A phenyl or naphthyl group, a phenylalkyl or naphthylalkyl group having 2 carbon atoms, a monocyclic or multiple ring group having 1 or 2 chlorine or bromine atoms, or 1 or 2 carbon atoms each having 1 to 2 carbon atoms a phenylalkyl or naphthylalkyl group substituted with 4 alkyl groups and having a total of 7 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 4 carbon atoms;
to 10 cycloalkylalkyl groups] An advanced epoxy resin obtained from the reaction of a diglycidyl ether of a di-secondary alcohol represented by (ii) a dihydric phenol. (2) Each R^1 is the same and each has 1 carbon atom
The resin according to claim 1, which represents from 1 to 14 alkyl groups, allyl groups, cyclohexyl groups, or benzyl groups. (3) R represents a group represented by the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^2 represents a methylene group or isopropylene group] where each R^1 represents the number of carbon atoms A resin according to claim 1, which represents 1 to 12 alkyl groups. (4) The resin according to claim 3, wherein component (1) is 2,2-bis(p-3-(butoxy-2-glycidyloxypropyloxy)phenyl)propane. (5) The dihydric phenol has the following formula: HO-X-OH [wherein, ▼(L is a direct bond, an alkylene group having 1 to 6 carbon atoms, and 2 to 6 carbon atoms.
The resin according to claim 1, which is represented by an alkylidene group or ▲representing a numerical formula, chemical formula, table, etc.)]. (6) The resin according to claim 5, wherein the dihydric phenol is bisphenol A. (7) Components (i) and (ii) are each 70 to 9
5% by weight and present in a concentration ranging from 30 to 5% by weight. (8) Claim 1, wherein component (i) is 2,2-bis(p-3-(butoxy-2-glycidyloxypropyloxy)phenyl)propane and component (ii) is bisphenol A. Resin listed. (9) (i) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a phenylene group or a naphthylene group, or one or two carbon-carbon bonds, an ether oxygen atom, Sulfur atom, sulfonyl group, sulfoxide group,
Represents a group consisting of two or three phenylene groups connected by a carbonyl group or an alkylene group having 1 to 5 carbon atoms, or a group consisting of 1 or 2 monocyclic or multiple rings each having 1 carbon atom by 1 to 4 alkyl groups or 1 or 2
each phenylene group or each naphthylene group substituted by chlorine or bromine atoms, and R^1 is independently a straight-chain or branched alkyl group having 1 to 16 carbon atoms, 1 to 4 carbon atoms; straight-chain or branched-chain alkyl groups having 1 to 16 carbon atoms substituted with chlorine or bromine atoms, straight-chain or branched-chain alkenyl groups having 2 to 6 carbon atoms, 1 to 4 chlorine atoms or a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, phenyl or naphthyl group, monocyclic or multiple rings substituted with bromine atoms, with one or two chlorine or bromine atoms, or one or substituted by two C1 -C4 alkyl groups and in total 6 to 1
A phenyl or naphthyl group, a phenylalkyl or naphthylalkyl group having 2 carbon atoms, a monocyclic or multiple ring group having 1 or 2 chlorine or bromine atoms, or 1 or 2 carbon atoms each having 1 to 2 carbon atoms a phenylalkyl or naphthylalkyl group substituted with 4 alkyl groups and having a total of 7 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 4 carbon atoms;
to 10 cycloalkylalkyl groups] A thermosetting resin comprising an advanced epoxy resin obtained from the reaction of a diglycidyl ether of a di-secondary alcohol represented by (ii) a dihydric phenol, and a curing agent therefor. Composition. (10) The thermosetting composition according to claim 9, wherein the curing agent is a melamine-formaldehyde resin, a urea-formaldehyde resin, or a phenol-formaldehyde resin. (11) Component (i) is 2,2-bis(p-3-(butoxy-2-glycidyloxypropyloxy)phenyl)
10. The thermosetting composition according to claim 9, comprising an advanced resin which is propane and whose component (ii) is bisphenol A, and a curing agent therefor. (12) (i) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a phenylene group or a naphthylene group, or one or two carbon-carbon bonds, an ether oxygen atom, Sulfur atom, sulfonyl group, sulfoxide group,
Represents a group consisting of two or three phenylene groups connected by a carbonyl group or an alkylene group having 1 to 5 carbon atoms, or a group consisting of 1 or 2 monocyclic or multiple rings each having 1 carbon atom by 1 to 4 alkyl groups or 1 or 2
each phenylene group or each naphthylene group substituted by chlorine or bromine atoms, and R^1 is independently a straight-chain or branched alkyl group having 1 to 16 carbon atoms, 1 to 4 carbon atoms; straight-chain or branched-chain alkyl groups having 1 to 16 carbon atoms substituted with chlorine or bromine atoms, straight-chain or branched-chain alkenyl groups having 2 to 6 carbon atoms, 1 to 4 chlorine atoms or a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, phenyl or naphthyl group, monocyclic or multiple rings substituted with bromine atoms, with one or two chlorine or bromine atoms, or one or substituted by two C1 -C4 alkyl groups and in total 6 to 1
A phenyl or naphthyl group, a phenylalkyl or naphthylalkyl group having 2 carbon atoms, a monocyclic or multiple ring group having 1 or 2 chlorine or bromine atoms, or 1 or 2 carbon atoms each having 1 to 2 carbon atoms a phenylalkyl or naphthylalkyl group substituted with 4 alkyl groups and having a total of 7 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 4 carbon atoms;
to 10 cycloalkylalkyl groups] A thermosetting resin comprising an advanced epoxy resin obtained from the reaction of a diglycidyl ether of a di-secondary alcohol represented by (ii) a dihydric phenol, and a curing agent therefor. A cured composition obtained by curing the composition at an elevated temperature.